Aqueous micellar and non-micellar effects during the asymmetric hydrogenation of dehydroamino acid derivatives: influence of amphiphiles on enantioselectivity and α-CH/CD exchange

The effect of different amphiphiles on the CH/CD exchange in the homogeneously catalysed asymmetric hydrogenation/deuteration of methyl (Z)-α-acetamidocinnamate or methyl α-acetamidoacrylate in an aqueous micellar medium has been investigated in connection with the effect of amphiphiles on the enhancement of enantioselectivity. In comparison with the exchange of α-CH/CD in water, the amphiphiles inhibit the reaction in the order: cationic